2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- CAS No.
- 84-58-2
- Chemical Name:
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- Synonyms
- 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE;4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile;Dichlorodicyanobenzoquinone;2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE;2,3-DICHLORO-5,6-DICYANOBENZOQUINONE;1,2-Dichloro-4,5-Dicyanobenzoquinone;Dichlorodicyanoquinone;2，3-Dicyano-5，6-dichlorobenzoquinone;2,3-dichloro-5,6-dicyano-4-benzoquinone;2,3,5,6-Dichlorodicyanoquinone
- CBNumber:
- CB5751792
- Molecular Formula:
- C8Cl2N2O2
- Molecular Weight:
- 227
- MDL Number:
- MFCD00001593
- MOL File:
- 84-58-2.mol
- MSDS File:
- SDS
| Product description | Number | Pack Size | Price |
| 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% | D60400 | 5g | $30.9 |
| 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% | D60400 | 10g | $55.3 |
| 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | D1070 | 5G | $35 |
| 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T) | D1070 | 25g | $104 |
| 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T) | D1070 | 250g | $632 |
| More product size | |||
| Melting point | 210-215 °C (dec.)(lit.) |
|---|---|
| Boiling point | 301.8±42.0 °C(Predicted) |
| Density | 1.7500 (estimate) |
| storage temp. | Store below +30°C. |
| solubility | Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane. |
| form | Crystalline Powder or Crystals |
| color | Yellow to orange |
| Water Solubility | reacts |
| Sensitive | Moisture Sensitive |
| Merck | 14,3063 |
| BRN | 747939 |
| InChI | 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13 |
| InChIKey | HZNVUJQVZSTENZ-UHFFFAOYSA-N |
| SMILES | ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O |
| CAS DataBase Reference | 84-58-2(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 1H5KD39UH7 |
| NIST Chemistry Reference | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2) |
| EPA Substance Registry System | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2) |
| UNSPSC Code | 12352117 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301 | |||||||||
| Precautionary statements | P264-P270-P301+P310-P405-P501 | |||||||||
| PPE | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 25-29-41-37/38-20/21-23/24/25 | |||||||||
| Safety Statements | 22-24/25-37-45-36/37-26-36/37/39 | |||||||||
| RIDADR | UN 3439 6.1/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | GU4825000 | |||||||||
| F | 21 | |||||||||
| TSCA | TSCA listed | |||||||||
| HazardClass | 6.1 | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29269095 | |||||||||
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
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| Hazard Classifications | Acute Tox. 3 Oral | |||||||||
| Limited Quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) | |||||||||
| Excepted Quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) | |||||||||
| NFPA 704 |
|
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone price More Price(51)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | D60400 | 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% | 84-58-2 | 5g | $30.9 | 2025-07-31 | Buy |
| Sigma-Aldrich | D60400 | 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% | 84-58-2 | 10g | $55.3 | 2025-07-31 | Buy |
| TCI Chemical | D1070 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | 84-58-2 | 5G | $35 | 2025-07-31 | Buy |
| TCI Chemical | D1070 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T) | 84-58-2 | 25g | $104 | 2025-07-31 | Buy |
| TCI Chemical | D1070 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T) | 84-58-2 | 250g | $632 | 2025-07-31 | Buy |
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Chemical Properties,Uses,Production
Description
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has a variety of applications. DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of quinolones and an oxidizing agent used to synthesize steroids. Additionally, DDQ is used with Ph3P to synthesize 1,2-benzisoxazoles.
Chemical Properties
yellow to orange powder
Uses
An oxidizing agent, especially in steroid synthesis.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.
Preparation
The first synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was described by J.Thiele and F.Guntber in 1906. However, no interest was shown in the compound until Linstead and co-workers discovered its extraordinary potency as a dehydrogenating agent. Its oxidation potential is greater than that of any other known quinone.
2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation
Application
2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be used as:
A deprotecting reagent for a variety of compounds, such as thioacetals, acetals, and ketals.
An electron-transfer reagent for the synthesis of quinolines from imines and alkynes or alkenes.
An effective reagent for the benzylic and allylic CH functionalization.
An oxidizing agent for the synthesis of functionalized furans and benzofurans.
A reagent with Ph3P in an efficient synthesis of 1,2-benzisoxazoles.
reaction suitability
reagent type: oxidant
Mechanism of action
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has many applications in the oxidation of various organic compounds such as ketones, alcohols, phenols, aromatic compounds, heterocyclic structures, etc. Apart from that, the presence of two chlorine atoms and two nitrile groups on the benzoquinone ring may also behave as a potential chlorinating agent. Consequently, DDQ could act simultaneously as the chlorinating agent and the oxidant. It can also remove the protective functional groups during deprotections of different chemical entities. For dehydrogenation by DDQ, the mechanism includes the transfer of hydride to the quinone oxygen followed by the transfer of a proton to the phenolate ion[1].
Safety
DDQ reacts with water to release highly toxic hydrogen cyanide (HCN). A low-temperature and weakly acidic environment increases the stability of DDQ.
Purification Methods
Crystallise DDQ from CHCl3, CHCl3/*benzene (4:1), or *benzene and store it at 0o. [Pataki & Harvey J Org Chem 52 2226 1987, Beilstein 10 H 902, 10 II 635, 10 IV 3521.]
References
[1] Alsharif, Meshari A. et al. “DDQ as a versatile and easily recyclable oxidant: a systematic review.” RSC Advances 47 (2021): 29826–29858.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hangzhou Qiwei Pharmatech Co.,Ltd | 13282840061 | mw@qwpharmatech.com | China | 109 | 58 |
| Hebei Yanxi Chemical Co., Ltd. | +8618531123677 | faithe@yan-xi.com | China | 5853 | 58 |
| Firsky International Trade (Wuhan) Co., Ltd | +8615387054039 | admin@firsky-cn.com | China | 427 | 58 |
| Capot Chemical Co.,Ltd. | +86-（0）57185586718; +8613336195806 | sales@capot.com | China | 29735 | 60 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21595 | 55 |
| Zjartschem | +86-571 87238903 | jocelynpan@zjarts.com | CHINA | 988 | 58 |
| Tianjin Zhongxin Chemtech Co., Ltd. | 86-22-66880623 +8618622897568 | sales@tjzxchem.com | China | 572 | 58 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29830 | 58 |
| NINGBO INNO PHARMCHEM CO., LTD. | 13867897135 | sales@nbinno.com | CHINA | 923 | 58 |
| Jinan Finer Chemical Co., Ltd | +86-531-88989536 +86-15508631887 | sales@finerchem.com | China | 2951 | 58 |
Related articles
- Application of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)
- DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of qu....
- Feb 16，2022
View Lastest Price from 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-03-06 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
|
US $0.00 / Kg/Drum | 1KG | 99% | 200mt/year | Jinan Finer Chemical Co., Ltd | |
 |
2025-12-03 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
|
US $10.00 / Kg/Drum | 500KG | 99% | 10T per month | Great Innovation (Shanghai) Pharma Co., Ltd. | |
 |
2025-11-18 | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
|
US $1.10 / g | 1g | 99.0% Min | 100 Tons | Dideu Industries Group Limited |
-
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
- US $0.00 / Kg/Drum
- 99%
- Jinan Finer Chemical Co., Ltd
-
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
- US $10.00 / Kg/Drum
- 99%
- Great Innovation (Shanghai) Pharma Co., Ltd.
-
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
- US $1.10 / g
- 99.0% Min
- Dideu Industries Group Limited
